


The Upper Hell Side

by screwdestinyintheface



Category: Gossip Girl, Supernatural
Genre: Alternate Universe, Alternate Universe - High School, Bottom Castiel, Bottom Dean, Cliche, Dean likes dogs, Drunk Sex, Explicit Sexual Content, Fluff, M/M, Masturbation, New York City, Romantic Comedy, Sexual Tension
Language: English
Status: In-Progress
Published: 2013-10-09
Updated: 2013-12-13
Packaged: 2017-12-28 23:13:12
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 3,415
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/998055
Author URL: https://archiveofourown.org/users/screwdestinyintheface/pseuds/screwdestinyintheface
Summary: <blockquote class="userstuff">
              <p>Crowley and Naomi Novak are 'King and Queen' of the Upper East Side in New York City, Castiel is their rebellious son who takes a like in the guy that agreed to walk their dogs.</p>
            </blockquote>





	1. It Had To Be You

**Author's Note:**

> Abandoned for now.

Dean angrily walked around in the heart of New York City. He just got lectured by some posh school principal, because he threw a fit in class when Gordon Walker insulted his little brother. He got kicked out again and is now walking around in the late summer heat, clothes sticky. The ridiculous uniform he was wearing was way too hot for this time of the year and he loosened his tie to open up the top buttons of his dress shirt. 

John, his father, wanted his sons to finish school here while he was out working some job. Dean was already in his last year, but he figured it was actually all for his little brother Sammy. He was the one that had pointed out the private school to John eagerly. He wanted to study Law later on and going to this particular highschool would get him the best recommendations possible. The only thing Dean wanted was to finish school and get out of this place again as quickly as possible.

John had dropped them off to stay with Ellen Harvelle, a friend of the family. It wasn’t that Dean didn’t like Ellen, hell he loved her like she was his own mother, but there was something about New York he didn’t like. For example the fact that he’d almost died a couple of times already due to reckless people on bikes or crazy taxi drivers. Plus his classmates weren’t anything like he’d ever experienced. They were the rich kids, socialites who held dinner parties and brunches, obsessed with their own reputations. How John was able to afford this all was beyond him. 

Dean was considering to get a snack on the way home when a big, blonde Labradoodle passed by. The dog was leashed up and pulled its owner through the mass of people. The guy was clearly holding on for dear life and tried to pull a Chihuahua, complete with pink jacket, along too. The poor thing looked just as uncomfortable as Dean felt himself. The owner looked friendly, he was almost as tall as Dean, with dark, messy hair and a lean body. Dean stared at the guy’s Nantucket red shorts for a moment with a frown, who the hell would wear pants like that? 

While Dean was staring, the Labradoodle suddenly arched his back and left a dump on his owner’s leather sandal. It was almost like he did it just for Dean’s sake. 

“Alfie! No!” The guy shrieked out with a suprising gravely voice and at that moment the dog decided to take off. The dog, Alfie, zigzagged through people’s legs and ran around the corner. Without thinking Dean started running to catch the pup before it got run over by some MTA-bus. 

“Buy a leash!” A woman’s voice called out behind Dean, but he managed to catch Alfie right before it wanted to cross the traffic on Fifth. Blinking up at Dean, wagging its tail, he looked like they just played a fun game of tag or something and Dean sighed. “It’s okay.” He whispered and took a strong hold of the leash. When the animal tried to lick Dean’s face he laughed bitterly; at least he made one new friend today. 

“Now I know you didn’t want to stay with him, but I gotta bring you back now okay?” Dean pulled Alfie along and around the corner, where the owner was still desperately trying to clean off the shit on his sandal with a plastic bag. The little Chihuahua had circled its leash around the guy’s legs so he was trapped. 

“Here’s your dog, although I don’t think you really deserve him.” Dean said with an eyebrow pulled up and the guy turned just as red as his shorts. He was goodlooking, Dean noticed, if he would fall for those rich, Upper East Side-types of course. 

Alfie sat down beside his owner and looked up hopefully. The guy held out his hand to Dean, but then thought better of it when he realised it was the one holding the bag of shit. “I’m sorry, normally I would shake your hand but...” He shrugged. “My name’s Castiel Novak. And these monsters...” He looked at his dogs who were now perfectly fine, sitting and looking up at Dean. Honestly they didn’t look like monsters at all. Not even the little one in the pink jacket, Dean thought. “Are Alfie and Meg. I promised my mother to take care of them for a few weeks.”

“Dean— I’m Dean.” He said with a slight nod of his head. Dean noticed now that Castiel (what kind of name is that anyway?) had the bluest eyes he’d ever seen, but pushed that thought far away. He didn’t even know why he was still here talking to the guy. 

“I think we started off on the wrong foot a little bit.” Castiel said while laughing and looked at his in poop covered toes. Dean pulled up both his eyebrows in surprise, maybe the guy wasn’t that bad. “So you go to St. Jude’s right?” He continued with a nod at Dean’s uniform. Dean couldn’t help the blush he felt creeping up his neck, he felt like an advertisement walking around in the thing. “I go to Riverside Prep, in West Side, my last year.” 

Alfie lay down against Dean’s feet and looked up at him with brown eyes that reminded him a lot of Sammy’s. “Hey boy, ‘was nice to meet you.” Dean said and petted the dogs curly head. “Well, good luck with ‘em.” He said hesitantly, looking into Castiel’s eyes once more before walking away. 

“Hey wait!” Castiel called after him. “You know, the dogs seem to really like you and I need help. The women who normally walks them ran off with the gardener.” 

Dean stopped. Was this guy joking? Still, he was curious and turned around. 

“No really, it’s actually kinda cute. They got married last week and are on their honeymoon to Niagara Falls now. But now I’m responsible for the dogs and I—Will you help me?” 

Castiel’s insanely blue eyes seemed honest, but Dean opened his mouth to say no. Did he really expect Dean to do his dirty work? 

“You’ll get payed of course!” Castiel suddenly added and a crooked smile broke out on his face, like money didn’t matter to him at all. 

Dean thought about it. The guy may or may not be a douche, but the dogs were actually pretty cute (you know, for dogs!) and it wasn’t like he had anything else to do with his spare time. The money would come in handy too. "Okay.” Dean said, still slightly hesitating. “I’ll do it.”

Castiel’s face immediately seemed to radiate happiness, but continued very business-like. “Great, you owe me! Can you be at my place tomorrow around three? I live on Sixty-eight on Fifth.” He pushed a thick business card into Dean’s hands and smiled. 

The guy had his own business card. Dean took a look at it and expected some lame title, but the card just stated his name and adress, black on white. He lived in the penthouse of The Novak Complex. Of course Castiel had the same name as the building. Naturally. 

“Then I’ll see you tomorrow Dean!” 

Dean had no idea what the hell just happened, but when he turned to walk away one of the dogs started to whine softly. Castiel Novak. He’ll ask Ellen if she knows the family.


	2. Take A Chance On Me

Dean couldn’t suppress the loud yawn he let out during the last hour of school. The others in class snickered at his reaction and Dean rolled his eyes, he could care less what they thought of him. Who cares anyway? It was the last hour of their day, and they were discussing The Great Gatsby by F. Scott Fitzgerald and Dean was simply... not interested. 

The way how all his fellow students told about the book in excitement made him want to pull his own hair out and he bit on his tongue to keep himself from cursing. The principal had said that they weren’t going to give him a lot of chances anymore, and if he misbehaved one more time, he’d have to do some weird volunteer job to compensate. Which is something Dean really doesn’t want to do. 

“Did you want to add something to our discussion, Mr. Winchester?” A bitter sweet voice called out above his head and Dean cringed at the sound of it. The stuck up teacher, Ms. Welch, was sitting on top of his table, looking down at him. You could definitely argue about the length of her skirt being too short for a teacher, and Dean tried his best not to glance down. 

He wasn’t crazy, he’d heard everything about a few ‘affairs’ that the young teacher was rumoured to have, all of them with her own students. Dean struggled to get one of his charming smiles on his face through his disgust and couldn’t believe his luck when he got saved by the bell. He grabbed his unused notebook and almost ran out of class to his locker, eager to get the hell out of this place. 

Now was the time for a lot of students to go to their extracurricular activities, so Dean was one of the only guys that walked towards the big blue doors of freedom (a little nickname he’d given them). He stopped for a second at the bulletin board though, to look over some of the club advertisements. Maybe the principal would give him another free pass soon if he showed some school spirit. 

DRAMA (Nope)  
FLOWER ARRANGING CLUB (Oh no)  
HOMEWORK CLUB (Hell no)

Dean shook his head, aren’t there any clubs for people that’d rather not be here or something? 

“You joining?” A familiar voice asked and Dean turned around with a smile when he saw his little brother, Sam, approach. “Hey Dean.” The younger brother added and stomped him gently in his stomach. Dean ruffled through Sam’s floppy, brown hair and laughed. Soon he was going to be taller then Dean himself, which Dean couldn’t wait for. His little brother just hit the awkward stage of puberty and was in the middle of a growth spurt (finally). Which resulted in long limbs, where Sam hadn’t gained full control over yet. 

“Nah, I don’t really see one that fits me.” He answered and shrugged. Sam was blushing for some reason and he looked incredibly happy. “How was your day?” He asked, curious. 

“Awesome!” Sam called out enthusiastically. “I invited some of my class mates to the Roadhouse tonight!” 

“Does Ellen know about this?” Dean asked immediately, narrowing his eyes. Why hadn’t Sam told him this sooner? They both had been home last night, but Sam had been in his room. He didn’t even come out for their first authentic New York pizza. 

“Yeah, it was alright.” Sam said quickly, he gestured to the big plastic bag in his hands. Dean recognized it had some brand name on it, but he couldn’t care less about that. “These are the invitations, do you want one?” Sam started reaching inside the plastic to get whatever kind of invitation out, but Dean quickly pushed his hands away. 

“No thanks, I don’t want one of your geek-invitations. What are you guys gonna do anyway? Homework?” Sam’s face turned into an adorable version of his bitch-face, and Dean couldn’t resist chuckling. 

“No.” Sam rolled his eyes. “We’re just going to hang out. Will you be there too?” Sam’s almost-bitch face turned into something that you could easily compare to a puppy begging for food, and Dean let out a sigh. 

“Sure. I’ll be there.” Dean answered and pretended to be very interested in one of the red propaganda-like posters on the wall. He didn’t like the friends Sam was making at all. They were all stuck up, spoiled brats, who hadn’t done anything else but party in their life yet. 

“Okay... I’ll see you there then.” Sam said a little awkwardly, like they hadn’t known each other all their lifes. Dean saw him wave out of the corner of his eyes, before walking away. 

Finally walking through the big, blue doors of freedom, Dean put his hands in the pockets of his slacks. He felt something hard with his left hand, took it out and looked at the ivory coloured business card in his hands. Had the guy been serious about walking their dogs?

It wasn’t like he had anything better to do. 

Dean walked over Fifth, until he reached the adress that was stated on the card. He looked up to see a building worthy of being called a skyscraper, a pair of golden wings spreading themselves above the doors. ‘NOVAK COMPLEX’ it said in big, golden letters, and Dean rolled his eyes. It was even worse then he had imagined. 

Inside, the doorman sat behind an impressive black desk. He was wearing an excessive blue uniform, with golden tassels on his shoulders and stomach. The man was old, and looked like he had been wearing the same uniform since he was 16. 

“I’m here for this guy.” Dean told him, and slid the business card over the desk. He would never get used to doormen. 

“The private elevator is the one all the way in the back on the left.” The doorman said and smiled a grandpa-like smile. Dean smiled back and once he got into the elevator, he pushed the button for the penthouse. He held in his breath as the elevator shot up 26 floors. The doors opened and Dean walked right into the apartment. 

Castiel stood in the middle of a hall that looked like someone had puked gold all over it. Castiel had the little chihuahua (Meg, right?) in his arms and when he saw Dean enter the hall, his face lit up. His hair was a total mess, like he just took a nap, and he was wearing a pair of beige khaki pants. He held one of Meg’s paws up and waved it at Dean, like a little girl would do with a doll. 

“You came!” Castiel said friendly.

“Well, I’m actually here for these guys aren’t I?” Dean murmered and strode over to where Castiel was standing so he could take Meg from him. Curling his fingers behind the dog’s ears, Dean smiled as she attempted to lick his face. 

Alfie soon came running around the corner, wagging his tail like a mad man. Dean chuckled as the big dog almost slid towards them over the smooth floor. He actually felt better than he had all day. Putting Meg down next to her friend, they both looked up at Dean expectantly. 

“So, did you sleep off the load of shit from yesterday?” Dean couldn’t help himself, he had to ask, and it got even better when he saw that Castiel was blushing. He really seemed like one of those neat guys Sam would want to hang out with. Dean himself always liked to think ‘bad-boys’ were more his type. 

“Yeah, thanks for bringing that up.” Castiel said sarcastically. 

Dean looked behind Castiel, to see that the hall they were in bordered a lot of rooms. A lot. It actually looked like he saw a basketball court in one of the rooms on the left, but he didn’t have the time to take a closer look, an older woman entered the hall with lots of noise from high heels. 

“Castiel? Ah, there you are.” The tall brunette called out and stopped inbetween Dean and what Dean assumed was her son. Her hair was pinned up in a way that made her look more like a librarian, but Dean was sure that it was probably very ‘in fashion’. Or something like that. 

“This is my mother, Naomi.” Castiel pointed out to Dean. “Mom, this is Dean. He’s going to walk the dogs.” 

Naomi didn’t seem very impressed with the pressence of Dean, but was very eager to talk about her son. “Yes, Castiel is mine, isn’t he beautiful?” She proceeded to give Castiel a smooch on his tanned cheek, leaving behind a red lipstick stain. 

“Nice to meet you.” Dean said politely, trying to hold back his laughter. He looked at Castiel, mischief probably clear in his eyes, and resisted to take his phone out for a picture. “You’ve got beautiful dogs!” Dean added hesitantly, but he’d made the right call.

“I know!” She said, and smothered Alfie with a perfume heavy hug, her round ass sticking out. “They’re like my own children. Only difference is that they, unlike this boy over here, will always need there mommy.” Dean chanced a look at Castiel, but he just stood there with a sheepish smile on his face, and shrugged.

“I always need you.” A deep voice with a British accent called out behind Dean, and he turned around to see a short, dark haired man approach. The man gave Naomi a suggestive look and Dean had to fight the urge to make gagging noices. 

“I’m Crowley.” He introduced himself to Dean and grabbed his hand, pumping it up and down agressively. Dean saw how the man took everything in, from his uniform to his shoes, and for some reason Dean thought that this man knew exactly that Dean didn’t belong at the St. Judes. Nerves filled up Dean’s stomach, annoying him, why didn he even care what these people thought of him? 

“Hey dad... This is the Dean I told you about.” Castiel started.

“Dean who?” Crowley asked and Castiel shot an unsure look at Dean. 

“Um, Winchester, sir.” Sir? What the hell was he thinking?

“Like the gun, Winchester? Well, I hope you’re a top shot then!” Crowley said, another deep noise coming out of him. Dean assumed he was laughing, so he awkwardly smiled back. “So you’re going to take care of the bitches?”

“Um, yeah.” Dean said, uncomfortably. It was like he’d walked into some sort of lame, scripted reality show. 

“I think it’s better if Dean got started now.” Castiel suddenly interrupted, and Dean shot him a grateful look, the sooner he got out of here, the better. Castiel handed him two matching leashes, both covered in their expensive brand names. “I still have something for you in the kitchen, and then I’ll walk you to the door.”

They left Castiel’s parents (thank god!) without any goodbyes and walked through a curvy corridor. The paintings on the walls were splattered with green dots, and it made Dean think strongly about buggers. 

“I’m sorry about them, they weren’t supposed to be home.” Castiel told him when they finally reached the kitchen. Dean looked around the ultra modern thing, and was too afraid to touch anything. A white mug with golden wings on it, the same as the ones on the building, was handed to Dean, and he pulled up his eyebrows in surprise. 

Coffee. Black. Exactly how he always drinks it. 

“I thought you could probably use it after a day of school.” 

Dean had to shake himself after a few seconds (minutes?), ‘cause he’d been officially lost in those stupid blue, earnest eyes before him. He took a sip and it actually made him think of home. Or whatever you’d call the car that you had spend your childhood in. 

“Thanks.” Dean said, almost agitated. “It’s really good.”

“Great. I didn’t know how you drink your coffee, so I had our chef Raphael make one for you.” Dean’s heart sank a little. Of course a damned chef had to make this. He didn’t really know why he thought that was bad per se, but he did. 

“Oh.” Dean murmered, and sat the mug back down on the counter. 

“I can come with you if you want?” Castiel’s gravelly voice sounded almost... hopeful? But Dean didn’t want his company, not now. 

“No that’s fine, I’ll manage.” Dean whistled on his fingers and not long after, Alfie and Meg came running. He put on the leashes, and walked back through the corridor with the bugger paintings. Castiel followed him close by. “See you later!” Dean called out, stepping into the elevator, not bothering to even look back at Castiel. He doesn’t really know why he’s acting like this, but the whole experience and being in the penthouse alone made Dean feel weird as hell. 

Back on the main floor, the doorman tipped his hat at Dean. 

“Au revoir, young man!”


End file.
